


Joining in the Fun

by Impala_Cherry_Trickster



Category: Supernatural
Genre: Accidental Voyeurism, Anal Sex, Angel Wings, Awkward Sexual Situations, Blindfolds, Bondage, Established Dean Winchester/Sam Winchester, First Time, First Time Blow Jobs, Grace - Freeform, Light Dom/sub, M/M, Multiple Orgasms, Orgasm Delay/Denial, Season/Series 11, Sex Toys, Soulmates, Threesome - M/M/M, Top Castiel/Bottom Sam Winchester, Top Dean Winchester, Wincest - Freeform, Wincestial - Freeform
Language: English
Status: Completed
Published: 2019-08-18
Updated: 2019-08-18
Packaged: 2020-09-06 18:49:29
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,280
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20296270
Author URL: https://archiveofourown.org/users/Impala_Cherry_Trickster/pseuds/Impala_Cherry_Trickster
Summary: Castiel doesn't mind the relationship between the Winchester brothers, until he walks in on something that Dean intends him to join





	Joining in the Fun

Castiel, despite being naïve about many things, was not ignorant to the relationship between the two brothers. He knew quite a lot about it, in fact. He knew that, up until Sam returning from the Cage, there had been nothing but brotherly love between them. He knew that the stress of losing Sam, of seeing his brother almost put a bullet through his own head, had stirred the feelings in Dean that he had kept hidden for so long. He also knew that it had been Dean to make the first move, and Sam who followed.

But it was hardly a surprise to the Seraph. Heaven had made them soulmates for a reason, and all of Heaven and Hell had presumed them lovers, until they so adamantly stated they were brothers. Castiel now saw the irony of the statement. They were indeed brothers, they never denied that, they just included the love that they shared into that title of brotherhood. So, Castiel knew about their relationship, even though they didn’t publicly announce it.

Things had changed slightly, now that they had the Bunker. Dean was no longer a Demon, the Mark of Cain had been removed, and they had managed to avoid the pain that Lucifer could have unleashed had they let him out. It was just after the trip to the Cage, Dean and Castiel arriving just in time to see Sam sprawled out, Lucifer smirking down at him with a look that promised many a millennia of torture.

Because of this, Castiel was allowing them time now they were back in the Bunker. He opted for a beer, putting on some music and relaxing back in his room. This was how he remained for some time, before deciding that he wanted to shower. The drawers in his room contained clothes, even if he did not usually wear anything but his suit and trench-coat. He picked out one of Sam’s shirts and a pair of Dean’s jeans, before heading to the shower.

Lathered up in soap with his hair a mess, Castiel heard his phone ringing. He swore slightly, a casual thing that he had picked up from Dean, and grabbed a towel. Looping it around his waist, he grabbed the phone and checked the caller ID, before bringing it to his ear.

‘Hello, Sheriff Mills.’ He fumbled blindly for some boxers, attempting to dress while holding the phone to his ear. He could have used Grace, but it seemed trivial to use it for something everyone else managed.

‘Cas, hey. I’m sorry for calling you, but the boys weren’t picking up.’ _I’m sure they aren’t, _Castiel thought slyly, but he then listened back to the conversation.

‘That’s alright, can I assist you?’ That didn’t sound quite how he hoped, and he wished he possessed some of the finesse that Dean and Sam had. It must come from being a human, he mused, attempting to put on a sock.

‘I think I’ve got a Hunt, but I don’t know what I’m looking at. I could do with you boys coming down, especially with Claire about to grab a shotgun and charge it.’ The mention of his Vessel’s daughter did worry him, because it felt obliged to look after her. Finishing pulling the leg of his jeans up, he agreed to go and get Sam and Dean, then to drive to see her. She seemed happy with that, hanging up after exchanging the usual pleasantries at the end, and the Angel pulled on a shirt.

He went to the room that Sam and Dean had made for them to share, a large room cleared out with a double bed. He still remembered the faces they wore when explaining to Cas that they were making a room that they would share. Castiel had just smiled slightly, he had been waiting for them to stop pining, or for Dean to stop pining, for so long. He rose his hand, knocked sharply on the door, not willing to walk in if he wasn’t appreciated. There was a brief pause, before Dean’s voice rang out.

‘Come in, Cas.’ Cas opened the door, then almost tripped over his own feet. He fell still, staring at the scene, trying to understand why Dean had allowed him in. His eyes seemed drawn to Sam, it was pretty hard to not look, and he saw the smug smile on Dean’s face. What Castiel couldn’t understand was why Dean invited him in, why he was allowing him to stare at Sam like this. Dean himself was seated in the chair in the corner, slouching with his jeans unbuckled, lazily opened.

Castiel forgot why he had come in. His eyes trailed over Sam, who was lying on the bed. His hands were tied to the headboard with what appeared to be rope, his feet in some sort of bar. His eyes were covered with a black material, headphones over his head. His mouth was gagged with some sort of ball, which Castiel stared at for slightly too long, feeling his eyes drift to the shiny saliva around the edge. They then drifted, very guiltily, down his bare torso, to the fact that Sam wasn’t wearing anything at all.

The Angel didn’t know what the ring around his cock was for, but it stood out against the red flesh. As he stared at it, the darker head weeping a clear liquid, the veins standing out along the side, the fuzz of hair at the base, he felt his trousers tighten. Despite not having much experience, Castiel knew what was happening. He’d never been with a male, not that gender mattered much to him, so staring freely made his mind spin. Below his straining erection was something blue, poking out from his hole. It was shiny and slick, and Castiel found himself curious. Whatever it was, it looked like it was the reason Sam was currently tugging at the restraints, lost in himself as he listened to whatever music was playing through the headphones.

‘He’s gorgeous, isn’t he?’ Dean asked with a look of adoration in his face, and Castiel blushed darkly. He shouldn’t be looking, yet he found it hard to look into Dean’s eyes when Sam looked so… enticing.

‘H…’ He cleared his throat, shifting his weight to try and alleviate the pressure between his thighs, ‘He is. I… I didn’t mean to disturb.’ Should he apologise? Dean didn’t seem angry at him for staring at Sam, didn’t seem to want to stop him from watching. Dean shrugged, flicking a controller in his hands. Sam made a muffled sound, arching up slightly, his cock twitching angrily. Castiel watched in awe, then looked to the controls Dean was holding. It must control the device that was inside Sam, the Angel figured, looking up at the Hunter.

Dean just stared back, a smile on his face and his green eyes searching Castiel, pausing on the obvious tent in his jeans. It hurt slightly, straining against the material, but Castiel wasn’t sure what he should be doing. He looked at Sam, perfectly still on the bed, apart from the slightest twitch of his hips or the bobbing of his cock. It was then that the Angel noticed an odd ball in Sam’s right hand, and he focused on that.

‘It’s his safeword. If he needs to stop, he drops the ball.’ That made sense, especially since he was gagged. Dean shifted in the seat, and Castiel’s gaze was drawn to the hand that was inside his jeans. Unsure of how to proceed, he looked to Dean for hints of what he was supposed to do.

‘Do you wish for me to go?’ Castiel asked, and Dean shrugged.

‘You can go if you want, or you could stay. Enjoy yourself.’ That suggested that he would be involved in whatever the two brothers were doing, and Castiel wasn’t sure how to feel. On the one hand, he loved both Winchesters, and the thought of joining them did excite him. But, although he knew how Dean felt, he didn’t know how Sam felt. In fact, the younger Hunter didn’t even know he was here yet, he was relying on Dean to keep him safe. And Castiel didn’t think he could ever do something like that, which Dean seemed to pick up on.

‘Cas, it’s always been us three against the world. Whatever this is, whatever you decide, that’s fine with me. And I assure you, it will be fine with Sammy.’ Dean was very protective over Sam, got jealous when anyone looked at him, let alone flirted. Yet he seemed relaxed with Castiel staring at Sam openly, and Cas gave a nod.

‘I don’t know what to do.’ He admitted, very unexperienced with all of this. Dean grinned, standing up and walking across to Sam. The Angel stepped back slightly, watched as the Hunter traced his fingers up Sam’s thigh, the younger shuddering and arching into the touch. He skipped over his crotch entirely, going up to his neck, then to the headphones. He removed them, then reached around to the tie behind his head.

‘Good boy, Sammy.’ Dean murmured, undoing the blindfold. Castiel hesitated when Sam’s gaze latched onto him, eyes widening slightly, but he didn’t make any attempt to fight. His eyes trailed down slowly, landing very obviously on Castiel’s too-tight trousers. Dean gave him a moment, like he was waiting to see if Sam would drop the ball, but he didn’t. Dean grinned, undoing the spreader bar between Sam’s legs, then his wrists. As the younger shifted, it was obvious that the toy inside him shifted, because Sam’s eyes widened slightly.

‘Sammy, fancy showing Cas here the joys of sex?’ The gag was removed as well, Sam crawling across the sheets towards him, and Cas stepped to the edge of the bed. He was quite unsure what to do, watching as Sam knelt in front of him, hands reaching for his belt. He paused, flicking his gaze up to Castiel, silently asking for permission. The Angel gave a shaky nod, letting Sam slowly unbuckle the belt, then undo the jeans. He pulled them down, the Angel kicking them off, then the boxers slid down slowly.

Castiel thought he should feel guilty, for how hard he was. But Sam just smiled, shuffling until his face was almost pressed to his groin, and Castiel fought the urge to move forwards. A hand reached for the base of his cock, then lips sealed around the head of him. Castiel groaned, head tipped back at the odd feeling of the wet warmth sealing him in. This was definitely a sin, but who was he to care? It was worth it, for the feeling of a tongue tracing up the underside of his cock, before pressing down on the sensitive spot at the head. His hand worked what his mouth currently wasn’t, stroking him up until Castiel felt a warmth in his stomach.

‘How long’s your refractory period, Cas?’ The Angel understood the words, but was struggling to think properly when Sam moved down, taking him right to the base, nose pressed to dark curls. Castiel instinctively wrapped a hand in Sam’s hair, tugging ever so slightly, which resulted in a moan from the Hunter. The vibrations on his cock felt delightful, and he fought the urge to start thrusting.

‘Angel… can… immediate.’ Castiel tried, watching in awe as Sam sucked him down, cheeks hollowed out and throat opening beautifully. His hands moved to Castiel’s hips, urging him to thrust, and he did, hesitantly.

‘Then let Sammy get you off. Then I’ll show you what that toy can do.’ Sam gasped slightly, and Castiel was certainly happy with that. His hips moved slightly faster, Sam’s throat going lax as he did so. The look on his face, the innocent eyes that were wide, pretty hazel staring up at him, the Angel groaned low and pumped his hips faster, desperate for something he wasn’t entirely sure of. One of the hands on his hips left, tracing up his thigh and reaching for his balls, soft touch pushing him over the edge. He barely contained the shout as a shudder raced up his spine, pushing his cock down Sam’s throat and holding his head in place as he came.

Sam dutifully swallowed down everything Castiel gave, licking his softening cock and cleaning every drop off. The Angel watched him do so, stepping back and heading for the chair that Dean had left. He slumped into it, panting as he tried to control his racing heart and the feeling of liquid-legs. Sam was being retied to the bed, but this time on his stomach. It gave the Angel the perfect view of the toy, the shiny spread of lube around the edge of the pink flesh. The gag was replaced, the ball picked up and Dean came back across.

When he offered the control to Castiel, the Angel stared at him in shock. He took it hesitantly, glancing down to the very simple controls. Up, down, and a circular button he presumed was the stop button. It was already on, but he hesitated over the up button. Dean grinned, moving round to Sam’s side and sliding off the ring that was constricting him. A whine was muffled behind the gag, and Dean chuckled slightly.

‘Only when I say so, Sammy.’ It was almost tender, the way that Dean assured his sibling, had it not been accompanied by the look of lust on Dean’s face. At some point he had lost the shirt, and was barefoot in jeans. Cas took the opportunity to shuck off the socks, then pulled the hem of his shirt over his head. He hardly had to worry about being exposed, his cock had been down Sam’s throat only seconds before.

‘Alright Cas, when you’re ready.’

It was such a pretty sight, and the buzzing was almost immediately replaced by Sam’s gagged sounds, muffled whines and pleas that Dean seemed to be drinking in. Sam’s body tugged at the restrains, both the bar that kept his legs apart while he was kneeling on the bed, and the wrists that were bound. A light sheen of sweat covered his body, and Castiel had a view of the toy, and below that, his almost-purple cock. As the vibrations turned higher, Castiel worried that Sam might actually pass out, his body fighting so hard to not break Dean’s word.

He didn’t realise he was rock hard until his cock hit his own stomach, Castiel surprised by how much the sight was turning him on. Dean was stroking his own dick lazily, like it didn’t bother him that much that Sam was seconds from exploding.

‘Okay Sammy, cum for us.’ The us made Cas smile, followed quickly by a groan as he watched Sam tense up entirely, spilling onto the sheets beneath him as his hips rocked forwards. It was a pretty sight, and the Angel had to press down on the base of his cock to prevent him cumming as well. Sam slumped down after he finished, Dean taking the control from Castiel’s hand and turning it off.

‘Front or back?’ Dean asked, walking across to pull the toy out of Sam. The Angel’s dick throbbed slightly as he watched the pink flesh try and tighten around the toy, refusing its exit, but eventually it was out. Long, thick, and ribbed. Sam shuddered slightly, a low moan slipping out from under the gag’s hold. It was then that Castiel registered the question, and just stared at Sam’s ass.

‘Back it is.’ Dean said with a laugh, chucking a bottle at him. He caught it, staring down at the lube, before understanding what Dean meant. He had never used lube before, but he spread it over his cock, wincing slightly at the coolness. Dean had kicked his jeans off, undone the spreader bar and Sam’s hands, and was crawling up in front of his head. Castiel didn’t waste time, got to the edge of the bed and reached for skin, hands gripping Sam’s ass.

He spread them slightly, not quite believing he was allowed to touch, before Dean was feeding his cock into Sam’s mouth. The younger groaned happily, moved forwards slightly into the touch, Dean’s fingers wrapping into his hair. Castiel positioned his hips slightly, watching the head of his cock slowly push into him. Sam now seemed torn between pushing back onto him, or forwards towards Dean. In the end, Castiel helped him choose by pushing in until he was fully seated, gasping at the tight heat around him. He wasn’t quite sure how long to give Sam to adjust, but found it was almost impossible to do so with Dean’s heavy thrusts, rocking Sam back against Castiel’s hips. He slowly did the same, hands reaching for his hips and wrapping around them, tugging them back sharply.

The bed creaked under the constant pounding, Sam moaning between them. Castiel was struggling to keep his Grace bound, felt it swirling behind his hold on it. As the heat in his gut built up, the incessant want to drive into Sam, push him down into the mattress and snap his hips until the fire burnt out, his Grace threatened to burst. Dean was groaning now, sweat beading at his forehead and his hips faltering, Sam gasping slightly and his throat working. Dean sunk back just as Cas lost control, Grace bursting through his body.

The lamp in the room shattered, Grace flooding into Sam’s body before he could stop it. It wouldn’t hurt him, centred on all of them nerve-endings and traces over the most pleasurable spots in the body. Unable to control the action, his wings spread out, black, broken feathers stretching out as he pistoned his hips twice more before groaning, Sam tightening around and a scream breaking from his lips as the Grace targeted his cock.

Castiel collapsed on top of the Hunter, narrowly avoiding squashing him by moving slightly to the side. Sam had fallen still under him, Dean was now moving to the other side of them. Castiel flicked his hand, replacing the bulb he had broken, the light now showing the mess they had made. Sam was completely still, except from the rise and fall of his chest. One of Cas’s wings was resting over him, ending on Dean’s thigh, the other hanging off the bed.

‘Could you clear us up, Cas?’ Dean asked, gesturing to the wet sheets that Sam was unconscious on. Castiel did as asked, then was surprised when Dean pulled the sheets up around all three of them, including Cas’s wings under it. His fingers brushed through the black feathers lightly, made visible for the first time.

‘G’night, Cas.’ Dean settled down, wrapping an arm around his baby brother. Castiel moved down slightly, kept his wings over the two and shut his eyes as well, feeling the need to recover his Grace.

**

When he woke, it was because Dean was nudging him. Sam was curled up like an octopus around Dean, limbs entwined and his head tucked under Dean’s chin. The Angel looked to Dean, who smiled softly.

‘What did you come in for, Cas?’ It was then that he remembered Jody’s call, telling Dean about what she said. He listened, before rolling from the bed carefully, saying he would give her a call. He left the room, Castiel looking to Sam as the Hunter instinctively flinched on losing Dean. Still asleep, he rolled over, arms wrapping around Castiel and tucking under his wing. The Angel watched it happen, smiling down at him softly. Maybe this would work, maybe this was okay.


End file.
